o-Nitroacetanilide (o-NAA), an organic crystal, was synthesized and fully characterized by means of single-crystal XRD, FTIR, UV–visible,¹H and ¹³C NMR spectroscopic techniques. Its molecular structure was optimized, the subsequent electronic properties, the spectroscopic spectra were quantified using quantum chemical computations by density functional theory calculations and compared with the experimental results. Furthermore, the Mulliken atomic charges were estimated andthe molecular electrostatic potential map was plotted in order to identify the chemical reactive sites. To study the nonlinear optical (NLO) activity of o-NAA, the electric dipole moment, the static and dynamic polarizability and hyperpolarizabilities were computed indicating that it could be considered as a good candidate for NLO applications. The hydrogen bonding and the non-classical intermolecular interactions were investigated by performing a Hirshfeld surface analysis and their contributions were analyzed via the 2D-Fingerprint plots, thus revealing that the crystal structure of the studied molecule is mainly built up of H…H, H…O/O…H, H…C/C…H and C…O/O…C close contacts. From the 3D-molecular energy frameworks analysis, the lattice energy of the compound was found to be − 95.15 kJ.mol⁻¹, and has exhibited stabilizing strong CH…O, NH…C, lp…lp, lp…π and π…π interactions.

o -硝基乙酰苯胺 ( o -NAA ) 是一种有机晶体，通过单晶 XRD、FTIR、UV-visible、¹ H 和¹³ C NMR 光谱技术合成和充分表征。其分子结构被优化，随后的电子性质，光谱通过密度泛函理论计算使用量子化学计算进行量化，并与实验结果进行比较。此外，估计了马利肯原子电荷并绘制了分子静电势图以识别化学反应位点。研究o -NAA的非线性光学 (NLO) 活性，计算了电偶极矩，静态和动态极化率和超极化率，表明它可以被认为是 NLO 应用的良好候选者。通过执行Hirshfeld表面分析研究了氢键和非经典分子间相互作用，并通过2D 指纹图分析了它们的贡献，从而揭示所研究分子的晶体结构主要由 H…H、H …O/O…H、H…C/C…H 和 C…O/O…C 密切接触。从 3D 分子能量框架分析，发现该化合物的晶格能为 − 95.15 kJ.mol ^-1，并表现出稳定的强 C H…O, N H…C, lp… lp , lp …π 和 π…π 相互作用。